


Loving Winchesters

by writer95



Category: Supernatural
Genre: Angst, Blood and Violence, Dean - Freeform, Demon!Dean, Detailed descriptions of torture, F/M, SPN - Freeform, Spn fandom, Supernatural - Freeform, slight romance, supernatural family
Language: English
Status: Completed
Published: 2017-04-28
Updated: 2018-01-28
Packaged: 2018-10-25 02:37:30
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 5,356
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10754997
Author URL: https://archiveofourown.org/users/writer95/pseuds/writer95
Summary: Summary: You finally managed to get yourself out of hell but strike a deal with Crowley; you torture someone for him he gets info on an ex of yours for you.





	1. Chapter 1

**Author's Note:**

> this fic is also on tumblr. http://deals-with-demons.tumblr.com/post/160037286390/loving-winchesters
> 
> Beta'd by the wonderful @whywhydoyouwantmetosaymyname (tumblr)

You walked down the decrepit stairs that led into the old leaden basement. It had been centuries since anyone last walked down into the basement of the old Victorian house; the house itself was old and weathered down. 

You tucked the small silver skeleton key in your back pocket; nobody needed skeleton keys anymore well except this house. You had refused to change the old locks to match the ones that were used these days; you liked the fact you only needed one key for every door it was more accessible this way. 

Getting down the last step you ran your hand through your short black hair; your dark blue eyes flicked black as you looked around. You had taken a dead body from the hospital as your vessel, the thought of sharing a mind with someone else felt outlandish.

Flipping on the light switch you were astonished when the small light bulb dangling off a rusted chain turned on. 

Memories flooded through your mind; the last time you had been down here was the night you went to hell. 

\----------------------------------------------------------------------------------------------------------------------------

You were sitting on your bed writing a note; you had been waiting for the demon to come and collect your soul when you heard the barking dogs. 

Quickly getting up you locked your bedroom door; not wanting anyone to come and try to stop the demon. Sighing you laid the note on top of your bed before running and hiding in the tall wardrobe that stood in one of the corners in your bedroom. 

You had remembered the sound of growling as the wardrobe had shaken; it wasn’t a normal sized dog after you. You had put your head on your knees and clenched your eyes shut waiting for what was to come.

The note had read; Dear mom and dad I’m sorry I couldn’t tell you that I would be parting ways with you today, please do not look for me because you won’t find me. I love you, I did this for you ten years ago and you raised me to hold up my end of the deal so please understand this is something I had to do. 

\----------------------------------------------------------------------------------------------------------------------------  
Everything was covered in dust now, you could tell it had been untouched for about ten years. 

Looking to the corner of the room was a pile of wood, walking and getting a closer look you sighed; it was the wardrobe you had hid in. 

Bending down you grabbed the small rusted doorknob, the wardrobe had been in your family since it had been built. Tossing the knob aside you stood back up and turned. 

On the full sized bed was an open photo album, pictures of you were spread out on your bed. Walking over and grabbing one you smiled as you rubbed the dust off of it; it was a picture from your prom night, your boyfriend’s eyes locked on yours when your mother had sneakily taken the picture. 

Picking up another one you sighed; it was your first day of college; you had already broken up with your boyfriend of six years. You hadn’t wanted to be with him when you turned twenty-one you knew it probably still hurt to hear about your death but it would've hurt more if the two of you had still been together. 

You had decided to stay in your home town so you could stay with your parents, they had been so worried about you; with all the murders and thieves running around. You had agreed to stay with them; secretly you hadn’t planned on moving out so soon anyway. 

You had heard from your father that your ex had gone to the marines after the break up. You had been sad but knew it was for the best, that way you couldn’t run to him and beg him to take you back and you knew he would have.

Laying the pictures back down you sighed; your parents had probably searched everywhere for you. You wished you would have been able to tell them; you knew they wouldn’t have approved or even believed you for that matter. 

On your eleventh birthday you remembered getting a high dollar computer, you remembered going to the bathroom at ten o’clock and hearing your father arguing with your mother about how they didn’t have the money. 

Your mother had said that she knew and that was why it was the only thing they had gotten you. You had felt bad and quietly left the house with a box that held the computer. 

You had meant to try to get the money back and instead found a man with red eyes willing to help. He had told you that he could help you with your problems and you could keep the computer, you had agreed not wanting to part with your birthday gift so soon.

You told him you wanted your parents to always have plenty of money; he agreed and told you that meant you had to lose your soul and part with them in ten years. 

It had made you feel scared but you agreed to it anyway; wanting the best for them. You had meant to tell them details but once your father got his raise you didn’t want to spoil his good mood. 

On your twenty-first birthday you had wanted to tell them everything; how you made a deal with a demon and that tonight was your last night. 

Your father had gotten a new yacht and wanted to take it out, he offered to take you but you couldn’t bring yourself to go; you didn’t want to make your parents watch you die.

So you had hugged both of them for as long as you could and told them goodbye and you loved them. You didn’t know when the demon was going to come for your soul; when you heard the dogs you panicked and ran. 

You turned the light off and walked back up the stairs and into the kitchen; you had wondered how long your parents stayed here before they figured you weren’t coming back. 

The stove had old grease stuck to the burners; your mother had loved cooking but hated the way grease would always end up everywhere. 

Running a hand along the counters you felt the thick dust underneath. It had probably been about ten years since this house has been empty. 

Stopping you picked up the note at the end of the long counter; wiping off the dust and cobwebs you opened it up:  
(y/n), in case you’re alive and come back, this house belongs to you. I’m sorry we couldn’t leave you anything else, I know how much you loved this place. Your father and I had to leave; we couldn’t be here anymore without you. If you’re reading this and are alive, I’m sorry to say it means we didn’t end up together. WE LOVE YOU! 

 

Quickly rolling the note in a ball you threw it in the small silver trash can; you had a feeling your parents made their own deal to make sure the house went to you. That’s why you had been given the small key when you finally climbed your way out of hell.

It had taken so many years of torturing and obeying to get out; and now your own parents were probably trapped in there the same painful way you had been. 

\----------------------------------------------------------------------------------------------------------------------------

You felt as if your legs and arms were being torn from their sockets, your wrists and ankles cuffed. Each tear that rolled down your cheek burned, your hair glued to your forehead and neck from your own blood.

Strangely, after twenty years of nothing but pain you were used to it. Even when Alastair used new methods, you sat there and let him torture you until it was time to be put on your chains.

“Tell you what, y/n, you can come off those chains and stop being tortured if you start doing the torturing.”   
“Okay.”   
Alastair grinned, “eager to torture, I like that.” The way he said it was sickening to you; it hadn’t been that you were eager to torture, you just wanted to be done.

At first, you thought it might be easy enough. They were in hell for a reason: they could have murdered or raped. But then you thought of how you were in hell; what if the people you had to torture were only down there because they wanted to help a loved one. 

The first few times were hard, the feel of the small scalpel in your hands when it was first handed to you. You had clenched your eyes shut as your fingers tightened around it. 

Opening your eyes and seeing your first victim you sighed; this person had never done anything to you but you wanted out of hell at all costs. You wanted to find your parents and tell them everything and apologize; you wanted to find John as well, to tell him you didn’t mean to cause him so much pain and you even hoped he was single so you could beg him to take you back. 

Taking a deep breath, you made a cut along the guy's chest slowly; you knew it hurt more the slower you went and you wanted to prove to Alastair you were ready for what he was asking in hopes that he would let you back on the surface. 

It had taken what felt like hundreds of years; you had come up with new torture methods and even enjoyed it. You had talked Alastair into letting you have the really bad cases.

“Looks like you got a ticket out.” You had just finished another session when Alastair handed you a small silver skeleton key; you had known instantly what the key went to, but were too confused and excited about leaving to ask questions. 

\--------------------------------------------------------------------------------------------------------------------------

You didn’t like the thought of your parents being in hell; hopefully John wasn’t in the same situation. You had hoped he had moved on: gotten married, had a family. 

You closed your eyes; secretly you wished he was still single and had been waiting for you all this time. You knew better than that. You had to let him go after all you had broken his heart.

You appeared in front of John’s place, well, the house he lived before he went to the Marines. You had spent so many days here with him. 

The wooden fence was leaning inward at the bottom and the gates were open and hardly on the fence. The paint on the house was chipping off, and the porch was weathered down so badly it looked like it would break if someone poked it. 

You appeared in his old room, looking for any clues as to where he might have gone if he had come back from the Marines. You didn’t want to think about him not making it home. If he died at war you would blame yourself. 

The room was pretty much empty with only a few things scattered on the floor; if he had been here, he left in a hurry. Bending down you picked up a small photo: it was a picture of him holding the hands of Mary Campbell. 

Great. You had wanted him to move on yes, but not with your best friend. You couldn’t believe that out of all the girls he could of chose, it was her. When you had last seen the two, they couldn’t stand each other and now they were a couple? 

What the hell did I miss.

You crumpled the picture up and threw it down. Appearing in your kitchen, you grabbed the newest phone book, looking for any Campbell or Winchester you could find. Having no luck you threw the book down.

“Ugh!”

“Hard day being back on earth, Love?” You turned to see the one and only King of Hell standing in the doorway that led to the living room. 

“Just looking for an old friend.” 

Crowley smiled, “I figured as much. I had no plans on you coming back so soon, but things happen.”

You rolled your eyes at the king, “you mean deals happen.” 

“Look, I’ll help you if you help me.” 

You sighed, “I really hate torturing.” 

He grinned, “you’ll like what I send you after. I hear you used to hunt with the best friend of yours.” You shrugged.

“Ex best friend.” 

“Ah you found out she was with your ex.” 

“What do you want me to do, Crowley?” He grinned 

“I have this vampire that just won’t stay away from my territory. I can’t have that now can I.” It was your turn to smile; the thought of torturing humans pained you, but monsters would be no problem.

“So, I rough up the vamp for you, he tells his friends, and you either get your territory back or a nest of pissed off vamps.” 

He nodded, “exactly. If you do that, I’ll help you find your ex-sweetheart.” You sighed as you thought about it. You didn’t want Crowley prying into your business, but you could use the help. 

It wasn’t like you were looking to get back with him, no you just wanted to make sure he was okay and that he didn’t get dragged into anything when he got with Mary. You hoped he had kids and a wife, well a wife that wasn’t Mary. You had loved your best friend, but she wasn’t good enough for John. Hell, you weren’t even good enough for John. At least you knew she wouldn’t hurt him. Getting him killed was what you were worried about.

Crowley stood there waiting for your answer, he leaned against the doorway, his red and black suit managing to stay wrinkle free. He watched you as you thought it over, on the off chance that you said no he could send you to hell. 

Sighing you nodded, “alright, fine. Where’s the vamp at?” 

He smiled, “that a girl. I’ll text you the address and the time I want you to show up.”

“Yes sir.”  
He was gone in a blink of an eye. It was going to take some time getting used to the fact you can do that. Sure you’d done it a few times already, but that didn’t mean you were used to it. 

You took the time to take a shower and change your clothes. You wanted to wear something a little more you. You put on a pair of tight black jeans, a light purple tank top, and a blue jean jacket. 

You were putting your hair into a ponytail when you got a text message. After finishing your hair, you picked your phone up and read the address. 

Putting your phone in your jacket pocket you appeared at the spot. You already had the torturing plan figured out. Crowley had said he had planned to use you because you could map out a detailed torture plan that worked in around two minutes. 

You carried a black backpack that was filled with syringes of dead man’s blood and knives. You were getting things set up in a barn, all the windows were open. All you needed was the sun and the vampire.

Crowley had told you he had someone bringing the vamp to you and that was all you needed to know. You had all the time you needed to get everything in place. 

The sunlight wasn’t going to kill the vampire and you knew it, but having a really bad sunburn in addition to being tortured, was going to hurt like a bitch, and that was all you needed. You had the ropes and chair ready when you heard the deep voice behind you.

“I got your vampire.” Turning you smiled; the man that spoke had beautiful green eyes and you could tell that this demon was in his original body. You couldn’t help but wish that you could have had yours as well. 

“Thanks just sit him down.” He nodded and shoved the vampire into the chair then leaned against one of the old wooden poles. You poured a little dead man’s blood on each rope then tightly tied them on his wrists and ankles causing him to grunt.

You then turned and looked towards the man, “if you’re going to stay and watch me, I’ll need your name” He smiled.

“It’s Dean.” 

You smiled back. “I love that name, mine is Y/N.” 

You then turned back to the vampire and closed your eyes; after you cleared your mind you opened them. Looking outside you watched the sun begin to rise; perfect. 

“I will be starting soon, so be sure to enjoy this time.” 

The vampire scoffed, “The sun won’t kill me.” You laughed; your voice sounding menacing. 

“Oh I know, but it will hurt.” 

You were organizing your tools while the sun rose and you could feel Dean watching you. The vampire wenced in pain, letting you know it was starting to bother him. 

You took out a small bowl that was filled with blood. Smiling, you covered one of the knives in it then turned to the vampire, “we’re going to do this very very slowly.” 

The slower the torture, the more effective. 

Walking to the vampire you ripped his shirt open then held the knife above his chest letting some of the blood drip down. Once the blood made contact, he groaned. 

“In case you don't know why this is happening to you, you and all your little buddies are in demon territory.” 

The vampire laughed, “torture me all you want, we won't be leaving anytime soon.”

You smiled. “I love it when my victims are stubborn, means more fun for me.”

You selected one of the syringes that was about halfway full, you then turned the vampire’s neck and and injected the blood in one of his veins. He screamed out in pain and you laughed. 

“For someone so stubborn you sure can’t hold your screams long.” 

He grunted and looked at you, “screw off! Why do you demons need the land anyways?” 

You shrugged, “I’m just here to torture you. I didn’t ask for details.” 

That made the vampire grin, “I see, you’re just the demon’s mindless minion.” 

You returned his grin, “oh no, sweetheart, I’m the demon’s torture mastermind.”

He scoffed, “yeah okay, whatever you want to believe, princess.” You almost growled; almost but didn’t.

That comment bothered you; but there was no way you were going to let him know. Instead you just smiled at him as you leaned closer; never breaking eye contact. Keeping the smile on your face you stared at him for what seemed like forever; once satisfied you gently cut down his chest then slowly deepen the blade as you went back up.

He screamed in pain and gripped the chair. You could see his nails scratching the old wood. His skin was starting to redden in the sun. 

Grabbing another syringe, a full one this time, you held his head and injected it behind his right eye. Both eyes closed as he screamed and grunted again; his body began shaking. You knew he wouldn’t be able to handle much more. 

You dabbed a bit of blood on your lips as if it were lipstick, then sashayed over to him and smiled, “you were too easy.” 

He looked at you confused, but before he could tell you that he hadn’t given in yet, you planted your blood soaked lips onto his dry ones. 

Holding him there for a minute you released him. He screamed, tears rolling down his cheeks. 

You smiled and lifted his chin so that he was looking at you, “there, there, it’s okay. Do you really want the rest of your family going through this?” 

He shook his head no. “I don’t want you anywhere near my sons.” You patted his cheek.

“That’s probably a good idea, you should leave and take your sons somewhere I can’t find you.” 

He nodded, “fine, you win.” You snapped your fingers releasing him; he left as soon as the chains were off. 

Dean clapped, “not bad, how’d you know that a vampire's nest is their family?” You grinned.

“I used to hunt with a friend of mine.” 

Dean stepped closer, “so, what landed you in hell?” 

“Made a deal that my parents would always have plenty of money.” Dean put a strand of your hair behind your ear.

“and then you were corrupted to torture.” 

You shrugged, “torturing monsters isn’t a problem.”

Dean nodded, “I understand that.”

“So how did you become a demon?” Dean showed you his arm, on it was a red mark. 

“The mark of Cain.” That explained how he kept his body. 

“That must suck.” 

He shrugged, “I like being a demon.” 

You laughed, “because you have no humanity to tell you you don’t? I hate it. I wish I was still human and with my parents. But if I hadn’t made the deal, I made we would be on the streets by now.” 

Dean looked at you shocked. “Really? You’d give up being a demon to be human?” 

You nodded, “yes.” 

Dean grabbed you and kissed you; you wanted to push away, but his lips felt so nice on yours. His green eyes closed as he deepened the kiss. You closed your eyes in return and wrapped your arms around his neck. You hadn’t been kissed since you were with John. 

It felt so nice, the way his tongue danced with yours, the way he lifted you up so easily. He pressed you up against one of the poles as the two of you were lost in one another. 

You didn’t think he would ever break the kiss, hell, you didn’t want him to, but as soon as someone cleared their throat, Dean broke the kiss and set you down. 

Dean turned, you moved to stand beside him and see who had entered and ruined the moment. 

“Well, I came to congratulate you on the victory, but I see Dean-O beat me to it.” 

Dean smirked and looked at you, “we can go somewhere else and finish what we were doing.” 

You wanted to say yes, but you weren’t even sure why he had kissed you. Before you could respond, Crowley spoke, “If you do go with him, you won’t get the end of our deal.” 

Dean rose a brow, “what deal?” 

Crowley smirked, “oh, you know, her wanting to know if her one true love is still alive.” 

You sighed, “my ex, okay. He wasn’t my one true love, I just wanted to make sure he moved on had a family, stuff like that.” 

Dean grabbed your hand, “I can help, what’s his name?” 

You were about to tell him when Crowley beat you to it: “John Winchester; he ended up with her best friend Mary Campbell, had two sons Dean Winchester and Sam Winchester; and yes the same Dean you were just kissing. Then of course, he sacrificed himself for the sake of Dean. Oh, and Mary burned on the ceiling checking on Sam when he was a baby.” 

Dean let go of your hand quickly. You didn’t blame him.

You looked at Dean. He did remind you a lot of John, but now wasn’t the time to compare.

“Well, I’ll leave you to your, uh, celebration.” Crowley was gone in a blink of an eye, leaving you alone with Dean Winchester.

Dean began to say something but you weren’t in the mood to explain yourself or or listen to what he had to say. You shook your head and appeared at your house. 

John had married Mary, had two son with her and eventually died. Mary died checking on her youngest. You sighed, you knew hunters lives were like that. That was one of the many reasons you never wanted him to end up with one.

After a few weeks you decided to go and find Dean, to apologize to him and tell him that what you and his dad had was in the past.

It took awhile to track him down, but you finally managed to do it. He was human and on a werewolf case. You sat back and waited for him and his partner to finish assuming his partner was his brother. 

“Dean, I’m sorry.” Dean turned. When he saw you, his lips tightened. 

His partner looked to him, “everything okay Dean?” 

Dean nodded, “yeah, Sam, it’s just, um she’s-,” 

You finished explaining to Sam: “a demon.” 

Sam straightened up and Dean looked at him, “it’s okay, she’s more of a hunter that tortures than a demon.” 

You smiled and nodded in agreement; Dean stepped closer towards you. You held up your hand. you wanted him to close the space and kiss you but a part of you wanted to tell him you couldn’t.

“Dean, I just came to say I was sorry; I didn’t come to fix things. I wanted to tell you that, as a hunter, you can’t be seen with a demon; that I’m sorry I let you kiss me before and that I was the one that let things go too far.” 

Dean scoffed, “you’re a demon that I happen to like. Hell, you straight up told me you wanted to be human and I know a way that can happen. I’m not gonna lie it’s pretty painful.”

Sam cleared his throat. “If my brother likes you, then I would be willing to help.” 

They reminded you so much of Mary, you sighed, “I don’t know, I just-” 

Dean kissed you, erasing whatever excuse you could come up with. He broke the kiss and you nodded, “alright I’ll do it.”


	2. Part Two

**Summary for the Chapter:**

> After agreeing to let the boys turn you back into a human you deal with the pain and memories of the process.

**Notes for the Chapter:**

> Beta'd by Alecai.  
> Warnings: Angst.  
> A/N: Please enjoy! Any and all feedback is greatly appreciated. If you have any questions or concerns feel free to message me!

After agreeing to turn back into a human, Sam had blindfolded you “No offense, but until your human I don’t want you seeing how to get where we live.” he explained as he tied the thick cloth over your eyes. “I understand.” you replied. 

Walking while blindfolded made you feel useless, you had to trust the boys and let them lead you as if you were a dog on a leash. Not that you had a problem trusting them, if they were anything like John then you were in good hands. If you were being honest with yourself it wasn’t that bad, relying on your hearing and smell was actually kind of fun to you. 

You had thought you would be able to get a little insight on the boys but as soon as you were in the car and moving someone turned on the radio, blaring classic rock. At first you were trying to ignore the music but soon found yourself singing along to Asia’s Heat of the Moment. 

Once the car stopped, one of them helped you out of the car. You heard a metal door being opened, after you were lead through it you heard it shut. Inside they helped you walked down a set of stairs, after making it down the stairs you walked a good ways before finally hearing the sound of something heavy sliding across the floor. Once they helped you sit down, they removed the blindfold.

As soon as they took the blindfold off you looked around, the room had very little lighting but enough that you could see the devils trap under the chair you sat in. You couldn’t help but wonder how many demons were tortured in the room, not like it mattered to you. You wanted to be human again, and if that meant being put in a chair in the middle of a trap then you could do it. 

“Now I must warn you that there is no guarantee we will be able to do this or that you will survive,” Sam informed you as he cuffed you to the metal chair. 

You thought about it a moment, On the off chance you didn’t survive you would probably be sent right back to hell. You could probably talk Alastair into getting your old job back. And honestly If you told them no they would probably think of you as any other demon. 

You wanted so badly to be human again, hell you were only a demon because of some deal you made when you were younger. You had to throw away your whole life for it, now Sam and Dean were giving you a second chance at a human life and by god you were going to take it. 

“I’ll take the chance” you assured him. 

Sam nodded as he set a black bag on the small table that was a few feet away from you. “Dean told me you knew dad and mom.” 

“I did, yes.” you gave a soft smile as you replied to Sam. 

Sam opened the bag and laid out a syringe filled with blood “What was my mom like?” You could see the wonder in his eyes as he asked the question. 

You wanted to tell him that he didn’t need to prolong the inevitable, but you could see that he really wanted to know. You felt bad for him, losing his mother when he was only a child and not getting to know her. 

Sighing you thought about what to tell him, you didn’t want to lie to him so you decided to go with the truth “She was fierce, not a force to be reckoned with.” 

Sam gave a small chuckle then sighed as he walked towards you “This will probably hurt.” 

You scoffed “I’m used to being tortured. I was in hell after all.” 

He tilted his head a bit as if to say ‘true’ then stuck the needle in a vein on your left arm. 

Once the blood hit your veins you couldn’t help but wince, it did hurt. It didn’t feel like any torture you had been through. It had burned, like your blood had been set on fire. 

Once he had injected the blood in your arm he set the syringe on the table by the bag and left, closing the doors behind him and leaving you alone with your thoughts. 

\----------

In your mind you could handle the burning sensation that the injection left, what you couldn’t handle was every bad memory of you torting a innocent person rushing through your mind. You were glad Sam left you alone, you didn’t want him to see you like this. 

Sam would come back and do the process again and again, each time the memories flooding in more vivid than the last. 

Hell you didn’t want to remember, you had hated what you had done and knew that no matter what you couldn’t take any of it back. 

You clenched your eyes shut, wishing it would all just go away. Instead it got worse, it felt like every memory was suffocating you. 

You started to feel like it wouldn’t work, like all the bad would outweigh any good and the transition would fail. Then you felt a rush through your skin, as if all the bad had vanished. 

Relieved, you couldn’t wait to test it and see if the demon was really gone. “Sam! Dean!” you hoped they would hear the excitement in your voice as you yelled. 

After a few moments of silence the doors opened, standing there was Dean and Sam. “Everything okay?” Sam began as Dean stepped into the room “Yeah is everything okay?” 

You nodded “I hope so, I think I’m human.” 

“Sam, go get the holy water.” Dean instructed, once Sam left he gave you a soft smile. “How are you feeling?” 

You chuckled, “Well, after all the burning it finally just stopped and I guess you could say I’ve felt better and worse.”

As soon as Sam was back he threw the holy water on you, not giving you enough time to even process it. Once it hit your skin all you felt was cold, no burning no stinging, just cold. “That’s really cold.” you couldn’t help but admit. 

Dean and Sam chuckled. “At least you didn't burn.” Dean added as he laughed. 

You nodded in agreement, “Very true.”


End file.
